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Four of six human monoclonal IgM proteins were found to react best with Klebsiella polysaccharides containing 3,4py β DGal (pyruvic acetalated D-galactopyranose), one with Klebsiella polysaccharides with 4,6pyDGlc; the sixth is uncharacterized. The combining sites of two of these (IgMWEA and IgMNAE) were essentially indistinguishable by quantitative precipitin studies at varying pH and by quantitative precipitin inhibition assays, but the other two differed in specificity of their combining sites from these and from each other. These differences were detected by precipitin inhibition assays with 3,4py β DGal-containing oligosaccharide alditols, the R and S isomers of methyl 4,6py α DGal, the R isomer of methyl 4,6py β DGal, or the R and S isomers of methyl 4,6py α DGlc, and -β DGlc. In all of these except the S isomer of methyl 4,6pyDGal and R isomer of methyl 4,6pyDGlc, the carboxyl group is axial to the plane of the acetal ring. Their specificity appears to be determined by the nonreducing ends of chains and is considered to be cavity-type.

NCBI PubMed ID: 6693372
Journal NLM ID: 2985121R
Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology

Klebsiella K12 capsular polysaccharide has been investigated by the techniques of methylation, Smith degradation-periodate oxidation, uronic acid degradation, and partial hydrolysis, in conjunction with 1H-n.m.r. spectroscopy at 100 and 220 MHz, and 13C-n.m.r. spectroscopy at 20 MHz. The structure has been found to consist of the hexasaccharide repeating-unit shown, having a D-galactofuranosyl residue at the branch point. In this series, a D-galactofuranosyl residue has previously only been found in the polysaccharide from Klebsiella K41.

NCBI PubMed ID: 7407803
Publication DOI: 10.1016/S0008-6215(00)84547-4
Journal NLM ID: 0043535
Publisher: Elsevier
Institutions: Department of Chemntry, The Umversrty of Brrtnh Columbra, 2036 Mum iMalI, Vancouver, B C V6T I Y6 (Canada)
Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, GLC-MS, partial acid hydrolysis, GLC, carboxyl reduction, Smith degradation, uronic acid degradation

Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans. Chemical synthesis of glycans bearing these functional groups or their variants is essential for the investigation of structure-activity relationships by a medicinal chemistry approach. To date, a broad choice of synthetic methods is available for targeting the different rare functional groups in bacterial surface glycans. This article reviews the structures of naturally occurring rare functional groups in bacterial surface glycans, and the chemical methods used for installation of these groups.

chemical synthesis, acetamidino group, amido group, bacterial surface glycan, carboxamido group, pyruvyl ketal

NCBI PubMed ID: 35750381
Publication DOI: 10.1016/S1875-5364(22)60177-8
Journal NLM ID: 101504416
Publisher: Beijing: Science Press; Elsevier
Correspondence: J. Yin
Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China